Potassium Iodide → 1,3-Dichloro-2-iodo-5-(trifluoromethoxy)benzene
Reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([Cl:14])[C:3]=1N.N([O-])=O.[Na+].[I-:19].[K+]>Cl.O>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([Cl:14])[C:3]=1[I:19]Participants
6
Conditions
- Temperature
- 40 °C
Procedure
2,6-Dichloro-4-(trifluoromethoxy)aniline (4.65 g, 13.2 mmol) suspended in 1 M of HCl solution (100 mL) was treated at 0° C. with sodium nitrite (0.913 g, 13.2 mmol) in water dropwise. After 15 minutes at 0° C., potassium iodide (2.20 g, 13.2 mmol) in water was added and the solution was heated at 40° C. for 15 min. The solution was quenched with saturated aq. Na2S2O3 solution (100 mL), and extracted with ethyl acetate (300 mL). The organic phase was washed with 0.1 N HCl solution satd. aq. NaHCO3 sol. (500 mL), and dried over sodium sulfate. Purification by silica gel chromatography (10-40% EtOAc/hexanes) afforded the desired product as a yellow solid.
Workup
- customThe solution was quenched with saturated aq. Na2S2O3 solution (100 mL)
- extractionextracted with ethyl acetate (300 mL)
- washThe organic phase was washed with 0.1 N HCl solution
- dry with materialaq. NaHCO3 sol. (500 mL), and dried over sodium sulfate
- customPurification by silica gel chromatography (10-40% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-a586d1e25e044628b792359eaab2f7b8
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563541B2
Reaction notes
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